4-Nitrobenzyl chloroformate → HCID 18620712, compound

HRID 1861710Notes

Reaction equation

HRID 1861710 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]([CH2:14][CH3:15])[C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1)(=O)C.[C:16](Cl)(=[O:28])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>Cl>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:17][C:16]([N:4]2[CH2:9][CH2:8][CH:7]([CH:10]([CH2:14][CH3:15])[C:11]([OH:13])=[O:12])[CH2:6][CH2:5]2)=[O:28])=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 782054-Nitrobenzyl chloroformateHCID 18621049HCID 18621049, compound

Product 1

HCID 18620712HCID 18620712, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent3×

Procedure

A mixture of (1-acetyl-4-piperidinyl)butyric acid (11.6 g, 54.4 mmol) and concentrated hydrochloric acid (30 ml) was refluxed for 16 hours, at the end of which time the hydrochloric acid was distilled off under reduced pressure. The residue was washed with ether and dissolved in 5N-NaOH/H2O (30 ml), followed by addition of ether (30 ml). To this mixture with ice-bath cooling was added p-nitrobenzyl chlorocarbonate (11.7 g, 54.3 mmol) in small portions, and the mixture was stirred at room temperature for 1 hour. This reaction mixture was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated NaCl/H2O and dried over MgSO4, and the solvent was distilled off under reduced pressure. The residual oil was treated with ether to provide the title compound (13.5 g) as colorless powders.

Workup

  1. distillationwas distilled off under reduced pressure
  2. washThe residue was washed with ether
  3. dissolutiondissolved in 5N-NaOH/H2O (30 ml)
  4. additionfollowed by addition of ether (30 ml)
  5. temperatureTo this mixture with ice-bath cooling
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with saturated NaCl/H2O
  8. dry with materialdried over MgSO4
  9. distillationthe solvent was distilled off under reduced pressure
  10. additionThe residual oil was treated with ether

Sources & evidence

ORD record
ord-cdc8be7c3eb34cffa14b3b88db4eb9c2
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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